


3 Times Team Free Will Wore Tuxes (+1 Time They Didn't)

by pieceofshir



Series: Pure Fluff [1]
Category: Supernatural
Genre: F/M, Idiots in Love, M/M, Tooth-Rotting Fluff
Language: English
Status: Completed
Published: 2020-12-24
Updated: 2020-12-24
Packaged: 2021-03-11 02:47:06
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,378
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28297752
Author URL: https://archiveofourown.org/users/pieceofshir/pseuds/pieceofshir
Summary: Pretty self explanatory I'd say
Relationships: Castiel/Dean Winchester, Eileen Leahy/Sam Winchester
Series: Pure Fluff [1]
Series URL: https://archiveofourown.org/series/2072676
Comments: 1
Kudos: 17





	3 Times Team Free Will Wore Tuxes (+1 Time They Didn't)

Number One: Dean

“I don’t see why it has to be me.” Dean grumbled, adjusting his tie in his bedroom mirror. Sam was lounging on his bed, smirking at him over his laptop. “Because Ryan Gaines invited you.” Sam reminded him, “And you need to be close, in case-”  
“-The vamps attack.” Dean finished, rolling his eyes. “Yeah, I know.” Sam scoffed at his brother, still fidgeting with his tux. “Dude, we wear suits everyday. What’s your problem?” Dean dropped his hands, turning to pin Sam with a glare. “This tie is green.” He deadpanned, as if that was reason enough.  
“Like your eyes.” Sam responded in a singsong voice, immediately ducking with a laugh as Dean threw the first thing he could find at his younger brother’s head. Slaughterhouse Five. “Let’s just get this over with.” Dean muttered, turning on his heel and storming out of the room. Sam scrambled to shut his laptop, hurrying after Dean.  
He caught up with him in the war room, where they had scattered books and files opened all across the table, documenting the pattern of the nest. They’d been hitting charity galas, and it just so happened that Dean had been invited by a cute journalist to this small Washington town’s annual fundraiser for LGBTQ+ youth across the state, and, well.  
Two birds, one stone.  
“You’ll be close by?” Dean picked up his knife, tucking it into his coat jacket. “Right outside,” Sam confirmed, “I promise.” Dean nodded, casting one final look at their scattered papers. “Right, then.” He was about to turn, when the familiar fluttering of wings made him freeze. “Hello De-”  
Dean tilted his head in confusion, turning to see Castiel standing, mouth slightly open, staring at him with wide eyes. “Uh, Cas?” Dean took a cautious step forward, waving his hand in front of Cas’ face. “Anyone home?”  
Cas’ mouth snapped shut, and he shook his head slightly, blinking rapidly. “Dean.” He repeated, “You, uh.” He looked the hunter up and down nervously, “You look...”  
“I don’t like it, either. But, y’know.” Dean shrugged, as if to say, ‘what can you do?’  
Sam looked between his brother and their best friend, scoffing lightly to himself. They’d literally managed to avert like, three apocalypses before those two could pull their heads out of their asses.  
“Why the...” Cas looked like it caused him real pain to say it, “the tuxedo?” Dean looked down, tugging on his jacket and mumbling something unintelligible. “What was that?” Sam piped up, shooting his brother a shit eating grin. Cas waited, and eventually Dean sighed. “I have a date.”  
The light overhead exploded.  
“Sonofa-!” The three ducked quickly as sparks and glass rained down. Dean looked around, confused. “I thought we checked the lights when we moved in.” Sam shot Cas a look, and at least the angel had the decency to look apologetic. “I guess we missed that one.” Sam shrugged, and Cas sent him a grateful smile.  
“I should get going.” Dean tried again, eyeing Cas warily, “Unless you had something to say?” Cas shook his head, trying not to look at Dean’s tie and how it matched his eyes. Dean nodded once, satisfied. “Come on then, Sammy.” He pushed past the angel, barely making it two steps before Sam spoke up again. “Hey, Cas, why don’t you come with?” He suggested, and Dean wished he hadn’t walked so far ahead so he could kick his idiot brother. “I...” Cas hesitated, sending Sam a panicked look, and he responded with an encouraging smile. “Okay.” He conceded, “I’ll...” he grimaced, pained expression back, “come with.”  
Dean rolled his eyes, turning back and continuing up the stairs. “Sam.” Cas muttered, grabbing his friend by the arm, “Sam, he’s wearing a tux.”  
“I know.” Sam gave him an encouraging pay on the arm.   
“His tie is green.”  
“I know.”

—————

Number Two: Sam

“Payback’s a bitch.” Dean hadn't stopped laughing since the email had arrived. Sam scoffed, finishing tying his tie before turning to Dean. “They’re friends from college.” He reminded his brother, “They think I left Stanford for Harvard Law, not... y’know.” He gestured vaguely, “All this.” Dean swung his feet off the bed, rolling his eyes. “Hey, weddings can be nice.” He tried, seeing how uncomfortable Sam was at the idea of lying to his old friends all night. “You got a date?”  
“Do I have a date?” Sam repeated, shooting him an incredulous look as they began to walk down the hallway, “Dude, how many girls do we even know?” Dean shrugged. “Nobody said you had to take a girl. Wanna borrow Cas?”  
“Borrow-” Sam huffed, glaring at Dean, who was looking back with a smirk. “I don’t want to borrow your boyfriend, Dean.” Sam looked smug at the way Dean flinched. “Besides,” they rounded the corner, heading into the library, “I can’t think of any hunter who would want to play house with me for a night.”  
“I thought you were going to a wedding.” Castiel put his book down, tilting his head in confusion, “Why would you be playing house?”  
Dean laughed loudly, clapping the angel on the back. “Sammy here is flying solo tonight.” Cas nodded slowly, not quite understanding but deciding to just go with it. “So you and I can-”  
“And Eileen.” Cas interrupted, causing both brothers to falter. “And Eileen?” Dean repeated, but before Cas could answer, the hunter in question appeared in the doorway, staring at Sam with wide eyes. “Cas let me in.” She said, and held up her mug. “I made coffee.”  
Dean turned to look down at Cas, who was fighting a smile. “What’s happening?” He whispered, eyes flicking between Sam and Eileen. Cas just shook his head, picking his book back up and standing, taking Dean’s arm gently. “Let’s go.” He whispered, tugging at Dean.  
“But-” He began to protest, but Cas just shushed him, pulling him back down the hall toward the bedrooms.  
Sam watched them leave, turning back to Eileen hesitantly. “I, uh.” He pressed his lips together, nodding at her, “I didn’t know you were coming.”  
“Neither did I.” She admitted, still eyeing him apprehensively. “But I was in Belleville hunting a wendigo, and I just really wanted-” She paused, stopping herself. “Dean’s cooking!” She blurted. “Cas texted me once about Dean’s burgers, and I just... really... I want one.” She trailed off, looking back at where Dean and Cas had disappeared off to. “So,” she finished, “here I am.”  
“Here you are.” Sam repeated. They stood in silence for a moment, before Eileen finally spoke, “So, tuxedo?” She gestured toward his outfit. “Yeah.” Sam looked down, “I, uh. Old friends’ wedding. You know.” He shrugged.  
“I do know.”  
They fell silent again.  
“You look good.” She offered, “Really, really... good.”  
Out of the corner of his eye, Sam saw Dean peeking out from the hallway, before he was yanked back, presumably by Cas. “Well,” Sam reached over, taking the Impala keys from where Dean had set them, “I should get going.”  
“Right.” She watched him give her one more smile, before turning and leaving. After a moment, she sighed. “You can come out now.” She called out, turning around to see that Dean and Cas were approaching her.   
“Burgers?” Dean asked, signing as he spoke. She nodded, and they shared a smile, before Dean turned, heading for the kitchen. Cas gave Eileen an understanding look. “Those Winchesters clean up quite nicely, don’t they?” He signed, sending her a wink.  
She laughed loudly, hooking their arms together and following Dean into the kitchen.

—————

Number Three: Castiel

In Dean’s defense, any time he saw Cas without that trench coat his brain sort of shorted out.  
But nothing could prepare him for the sight of the angel in a blue fitted tuxedo.  
A blue. Fitted. Tuxedo.  
He looked damn good, too.   
They were in Dean’s room, because the hunter had insisted that Cas couldn’t leave until he had voiced his approval. Problem was, he was seriously struggling to remember how to speak. “Dean,” Cas said, “you’ve been staring at me for nearly three minutes. Is there a problem?”  
Dean shook his head in an attempt to clear it. “You, uh.” His mouth felt entirely too dry. “You wear that well.”  
Cas turned to him with his signature head tilt. “I put it on correctly.” It wasn’t a question. Dean huffed a laugh, taking a step closer and brushing a piece of imaginary lint off his shoulder. “Yeah, you did.” Dean agreed, motioning for Cas to follow him to the common areas. “You’re sure you can handle this, right?” Cas nodded, resisting the urge to roll his eyes. “You want me to go to this auction, pretend to be a millionaire art collector, and distract the host while you and Sam sneak in to find the hex bags.” Dean’s eyes softened, and he reached out to adjust Castiel’s bow tie. “Just be safe, okay?” He tried to keep the worry out of his voice. “I don’t...” he trailed off, eventually deciding to drop it when Sam entered the room. “Okay,” He said, holding his phone out in front of him, “I’ll see you later. Yeah,” he chuckled, adjusting his earbud, “I’ll let them know. Bye.” He hung up, turning to the others. “Eileen says good luck, and she’ll try to drop by next time she’s in town.” Dean smirked at his younger brother, but he decided not to point out the way Sam’s ears were bright red. “You have got to marry that girl.” He said instead, laughing at the way Sam ducked his head, mumbling something that sounded suspiciously like, “I’m working on it.” Dean raised an eyebrow, but didn’t comment further. “You ready to head out?” Sam turned to address Cas, who was studying Dean. “Why don’t you go wait in the car, Sam?” Cas shot him a look over Dean’s shoulder, “We’ll be right behind you.”  
Sam nodded, catching the keys as Dean tossed them to him, and left to start the car. Dean waited until he could no longer hear his footsteps before turning back to Cas. “You were going to say something.” The angel demanded, “Tell me.” Dean faltered, deciding to play dumb. “No I didn't.” He said.  
“Yes, you did.”  
“Yeah, I did.”  
“So?” Cas looked at him expectantly. “You don’t...?”  
Dean hesitated. “I don’t...” He took a step forward, gathering his courage, “I don’t know what I’d do if you got hurt.” He admitted, “I don’t know if I can go through losing you again.”  
Cas smiled gently, taking one of Dean’s hands in both of his own. “I’ll be okay.” He promised, “I’m not leaving you.” Dean looked unsure, but before he could say anything, Cas leaned forward, pressing a gentle kiss to his lips. “I’m not leaving you.” He repeated, squeezing Dean’s hand. Dean stared, eyes wide in shock. “Okay, then?” Cas took a step back, tugging lightly on their joined hands so Dean would follow. He nodded, a smile slowly creeping onto his face. “Okay, then.”

—————

+1

Sam sighed, tossing his phone down onto the table. “Charlie’s out.” He turned to Dean and Cas, “She’s in West Virginia, following a wendigo. Says hi, though.”  
Dean groaned, hanging his head. “Is that all the women we know?” Cas asked, wrinkling his nose. “Just about.” Dean confirmed, “Unless you count Jody’s girls.”  
“Which we don’t.” Sam quickly answered, “Not for this.” They were silent for a moment as they imagined any one of those girls dressing up for a fundraising banquet to help women with disabilities.  
One where only women could get through the door.  
“Claire is technically Cas’ biological daughter,” Dean tried, “So maybe-?” “If I ask her for help on a hunt, none of us will ever hear the end of it.” Cas cut him off, “There has to be someone else.”   
“Are you boys still wasting time on this?” The three turned to see Eileen in the doorway, and Dean let out a low whistle. “Sweetheart,” he smirked, “if I wasn’t taken...”  
“If you want to continue being ‘taken’, you’ll end that sentence right now.” Cas grumbled. Dean winked at him, draping an arm over his shoulders. “You do look incredible, Eileen.” Cas finally agreed. She smiled at them both, turning to look up at Sam expectantly. “Well?” She asked, giggling at the way his jaw had practically dropped. “Uhh. Um.” He cleared his throat a few times, never taking his eyes off her. “Where did you even find that?” She shrugged, looking down at the red floor length dress she was wearing. “It was in a closet. I guess one of the Men of Letters had a lady friend.”   
“Friend.” Dean repeated, looking to Cas with a mischievous smirk. “You know,” he continued, quiet enough to make it seem like he was just talking to Cas, but loud enough that Sam knew he was supposed to hear, “If you think about it, you and I are basically ‘friends who only have one closet’.” Cas scoffed, smiling fondly, and the two settled in to watch as Sam continued to stumble over his words. “You... you really do look amazing.” She waited, knowing what was about to happen. “But,”  
“No, Sam.” She interrupted, eyes hardening, “No but. I can do this.” Sam hesitated, trying to find the best way to phrase it. “It’s just,” he turned to Dean and Cas for support, but it was clear they weren’t on his side. He looked back at Eileen, “You’d be going in alone. We wouldn’t be able to talk to you.”   
“I’ll have my phone.” She countered, “And despite what you may think, I can take care of myself.” Dean laughed loudly at that, giving her a thumbs up. “You tell him!” He called out, causing Sam to turn to him, glaring darkly. “Eileen.” Sam pleaded, “Sam.” Eileen narrowed her eyes, “I’m doing this.”  
“Sam.” Cas spoke up suddenly, catching their attention. He held up the flyer, pointing to the small print at the bottom. “You need a woman to get in.” He pointed, “But she can bring a date.”  
Dean nearly fell off his chair at the face Sam pulled. “Well that settles it.” Eileen smirked up at Sam.  
“Suit up.”


End file.
